I love having meaningful conversations about wealth, life design, and energy. They are pretty serious, high-stakes topics.
These are the three key factors to living a life you love and creating a lasting legacy: Wealth. Life Design. Energy.
I find myself thinking about legacy often. Sometimes, it feels exciting. Other times, it feels intimidating and heavy.
When I consider the bold moves my great-grandfathers made that led me to live the life I have today, legacy can feel like an obligation or duty.
My great-grandfather on my mother’s side, Biagio, came to America in 1913 from Italy. On a hope, a Catholic prayer, and a bit of honey bread, he made it to Sunnyside, Utah (the most misleading name for a town ever) where he started as a goatherd, then eventually became a coal miner.
It should be said that Biagio was the most cross-eyed man I ever saw, so it’s incredible that he had the vision to come to America. Perhaps if he could see better, he wouldn’t have settled in Carbon County, Utah.
Even though my grandparents were dedicated churchgoers, and both sides of my family were religious, there were things seemingly more important than church—like family, fun, and specifically laughter.
For example, my uncles (from both sides) were renegades. Crazy, wild, and HILARIOUS. I would secretly listen from the other room to the jokes they would tell, and if they were drunk enough, they sometimes would just tell them to me directly.
Our family gatherings were hysterical. Loud laughs. Long laughs.
At one of our family gatherings, I decided to repeat a few jokes I had overheard through the years, not knowing the meanings behind them, and I got laughs.
Wow! So, I could repeat the jokes my uncles had told and not get in trouble for being in appropriate or swearing?
The joke I told was, “Why did the chicken cross the basketball court?”
“Because he heard the ref was blowing fowls.”
They laughed, I didn’t know why, but I loved the feeling. The connection. The fun.
And now my youngest son loves to tell that joke too, so #legacy.
For decades now, when we have family events, everyone gathers around to tell jokes.
As a fourth-generation coal mining family (my great-grandfather, both grandparents, and my dad), I didn’t come from money—love and laughter were our currency.
I grew up in a small town.
A town that in its heyday had 5,000 people and 2 cops but is now 1,000 people and 5 cops—I guess things are going in the wrong direction. Sounds like a place where dreams go to die.
Last time I visited, I was greeted by a kid with a mullet on a BMX bike flipping me double birds. Home sweet home.
It wasn’t an easy place to make a living because it relied on coal mines, which come with lots of ups and downs. Mining disasters. Union strikes. And changes in coal prices and policy created uncertainty.
My family learned to hold tight to money.
My parents knew what it was like to live off water and saltine crackers during a strike.
We all deal with money, but too often, we do it poorly. And who wants the word “poor” associated with how they view money?
There is too little instruction and way too much fear…which ultimately leads to scarcity.
So, when approaching the topic of money and legacy, I thought back to when I was able to swear as a kid when telling a joke, but not in other situations, and realized that comedy allows me to tackle a critically important yet taboo topic.
Most people don’t find their legacy funny, or have a good chuckle over losing money. But is there a way to roast the system, laugh at the lies we’ve been told, and show just how hilarious and ridiculous the entire idea of money even is?
So that’s part of what legacy is. Sure, wills and trusts are part of legacy. Saving tax is part of legacy planning.
But the life we live, the path we chose, the purpose we discover, the time with family, the traditions and lessons too. These are all legacy.
I like to remind myself, I win when I play. Play removes the pressure, but fuels passion. Play creates moments, shared moments. It is living by example rather than trying to get everything right.
When I’ve made investment mistakes, had bumps in my business, or see my net worth decline, I worry that I am not being a steward over the opportunity my ancestors have provided me.
Yet, mistakes happen. We win or we learn (as long as we learn from the losses that is). Legacy isn’t about being perfect, it is about pursuing a life that we love. The life we don’t want to retire from.
For me it is listening to my intuition and going for it. My legacy is choosing to do comedy and bringing my kids and family along for the ride. Showing them I can pave my own path and it doesn’t have to be what society thinks is the best career or choice.
Legacy is a marriage of what I know and what I love to do. Of how I grew up, and what I grew into. Of who I am, and what I am.
By simply implementing the Rockefeller Method in my life (trusts and insurance), I have more permission to dream, to go for it, and no longer let money be the main reason I do or don’t do something. Money is a consideration, but not the main consideration.
I love having meaningful conversations about wealth, life design, and energy. They are pretty serious, high-stakes topics.
These are the three key factors to living a life you love and creating a lasting legacy: Wealth. Life Design. Energy.
I find myself thinking about legacy often. Sometimes, it feels exciting. Other times, it feels intimidating and heavy.
When I consider the bold moves my great-grandfathers made that led me to live the life I have today, legacy can feel like an obligation or duty.
My great-grandfather on my mother’s side, Biagio, came to America in 1913 from Italy. On a hope, a Catholic prayer, and a bit of honey bread, he made it to Sunnyside, Utah (the most misleading name for a town ever) where he started as a goatherd, then eventually became a coal miner.
It should be said that Biagio was the most cross-eyed man I ever saw, so it’s incredible that he had the vision to come to America. Perhaps if he could see better, he wouldn’t have settled in Carbon County, Utah.
Even though my grandparents were dedicated churchgoers, and both sides of my family were religious, there were things seemingly more important than church—like family, fun, and specifically laughter.
For example, my uncles (from both sides) were renegades. Crazy, wild, and HILARIOUS. I would secretly listen from the other room to the jokes they would tell, and if they were drunk enough, they sometimes would just tell them to me directly.
Our family gatherings were hysterical. Loud laughs. Long laughs.
At one of our family gatherings, I decided to repeat a few jokes I had overheard through the years, not knowing the meanings behind them, and I got laughs.
Wow! So, I could repeat the jokes my uncles had told and not get in trouble for being in appropriate or swearing?
The joke I told was, “Why did the chicken cross the basketball court?”
“Because he heard the ref was blowing fowls.”
They laughed, I didn’t know why, but I loved the feeling. The connection. The fun.
And now my youngest son loves to tell that joke too, so #legacy.
For decades now, when we have family events, everyone gathers around to tell jokes.
As a fourth-generation coal mining family (my great-grandfather, both grandparents, and my dad), I didn’t come from money—love and laughter were our currency.
I grew up in a small town.
A town that in its heyday had 5,000 people and 2 cops but is now 1,000 people and 5 cops—I guess things are going in the wrong direction. Sounds like a place where dreams go to die.
Last time I visited, I was greeted by a kid with a mullet on a BMX bike flipping me double birds. Home sweet home.
It wasn’t an easy place to make a living because it relied on coal mines, which come with lots of ups and downs. Mining disasters. Union strikes. And changes in coal prices and policy created uncertainty.
My family learned to hold tight to money.
My parents knew what it was like to live off water and saltine crackers during a strike.
We all deal with money, but too often, we do it poorly. And who wants the word “poor” associated with how they view money?
There is too little instruction and way too much fear…which ultimately leads to scarcity.
So, when approaching the topic of money and legacy, I thought back to when I was able to swear as a kid when telling a joke, but not in other situations, and realized that comedy allows me to tackle a critically important yet taboo topic.
Most people don’t find their legacy funny, or have a good chuckle over losing money. But is there a way to roast the system, laugh at the lies we’ve been told, and show just how hilarious and ridiculous the entire idea of money even is?
So that’s part of what legacy is. Sure, wills and trusts are part of legacy. Saving tax is part of legacy planning.
But the life we live, the path we chose, the purpose we discover, the time with family, the traditions and lessons too. These are all legacy.
I like to remind myself, I win when I play. Play removes the pressure, but fuels passion. Play creates moments, shared moments. It is living by example rather than trying to get everything right.
When I’ve made investment mistakes, had bumps in my business, or see my net worth decline, I worry that I am not being a steward over the opportunity my ancestors have provided me.
Yet, mistakes happen. We win or we learn (as long as we learn from the losses that is). Legacy isn’t about being perfect, it is about pursuing a life that we love. The life we don’t want to retire from.
For me it is listening to my intuition and going for it. My legacy is choosing to do comedy and bringing my kids and family along for the ride. Showing them I can pave my own path and it doesn’t have to be what society thinks is the best career or choice.
Legacy is a marriage of what I know and what I love to do. Of how I grew up, and what I grew into. Of who I am, and what I am.
By simply implementing the Rockefeller Method in my life (trusts and insurance), I have more permission to dream, to go for it, and no longer let money be the main reason I do or don’t do something. Money is a consideration, but not the main consideration.
If I have a character-building year (less profit), I know I have secured a death benefit that is guaranteed to pay tax-free when I die. This funds our Rockefeller Method family bank. It allows me to go for something that might take longer to develop or invest in a new way to do business that may not make as much money upfront. It gives me permission to dream and live without worrying about what I will leave behind. It is already secured and will fund the trust.
When money was the main thing, I felt more pressure. I have this once-in-a-lifetime opportunity created from generations of struggle from my ancestors. I used to think, “Don’t fuck it up.” Well, sometimes, that thought still enters my mind on a tough day.
That is when I remind myself to play.
To work out with my sons.
To date my wife.
To visit my parents.
To write, speak, or create something.
Last year I got in such good shape, six pack and all, that it impressed my sons. They are now working on their six pack, weighing every day, measuring their food and know all about macros. Legacy.
But legacy was also having my thirteen-year-old son open for my comedy show and crush it. Having all of my family in the audience for the filming of my comedy special. It was letting them in on the process and witnessing the struggle—having them see the work of going for a dream.
Legacy is the jokes we tell and the way we roast each other. We even have an annual Christmas Roast where we all share our comedy chops through videos, skits, gag gifts, and more.
Legacy is finding out my youngest son told my wife’s best friend’s daughter that I am a great example, I do life right, and he looks up to me. I cried when she told me.
Legacy is having my oldest son travel with me on book tour, work out with me a few times a week, and tease back and forth. Legacy.
Yet, I still have to remind myself of these things when I judge myself harshly for bad partnerships or selling my company for less than I could have.
I’m still human.
I’m still learning and doing work on myself.
The way most people view money or fear money or treat money is in opposition to legacy. Some are so cheap they miss out on memories that could have been created if they parted with some of those hard-earned savings. Others don’t unplug or take time away from work and miss out on beautiful memories and phases that come and go.
Part of the problem has to do with how we are trained when it comes to money and finance. I mean, whose fault is it?
Everyone wants to know how to make and have more money, but due to boring presenters, overly-complicated “expert opinions” and the same old tired advice of “just work harder” and “save more money.” people get frustrated and end up budgeting and cutting back and miss out on life, or they borrow even more just to get ahead, leaving them further behind and feeling defeated. It comes from faulty models and terrible advice.
This is where I am so excited about my mission, my future, and my living legacy.
Millions of people may want to be educated, but billions want to be entertained.
I get it so deeply and it is connected with every fiber of who I am, and what my family gave to me, so I wrote and performed “The American Ream,” a comedy special on Amazon Prime.
My methodology, advice, and message isn’t for everyone.
It’s not for people without a sense of humor that don’t want money for sure.
Definitely not for stubborn retirees, the Amish, those living in the woods with a bow and arrow and a loincloth…
And if people hate money, and enjoy being broke, stressed and miserable, then it’s probably not for them either.
Money matters because when people have an unhealthy relationship with money, people feel scared and often defeated. They have a constant weight of guilt, stress and shame hanging on them, dragging them down, and forcing them to give up the best of who they are in the name of paying bills. In the name of survival.
Sometimes it is debt that came with good intentions.
But we are all in store for financial surprises, it’s just when we’re unprepared, uneducated or unaware, that these surprises lead to money woes.
Maybe there was a change in the economy, or a decline in someone’s health, or a countless number of other factors, but until we can laugh about it, it is hard to learn, hard to face the truth, and most importantly, hard to heal and move on.
How can I do my part to help people close the wealth gap, heal from their money pain and mistakes, to take control of their finances, to get to the bottom of why they are in scarcity, fear, or debt and how to resolve it and prevent it from happening again?
First, be vulnerable and authentic.
Second, let’s laugh at money’s expense for a change (see what I did there, a pun).
Third, live my legacy instead of ruminating about each and every misstep, mishap, or mistake defining me (again, back to being authentic and vulnerable). See it as wins and lessons. What are the lessons? Share them. And tell some self-deprecating jokes along the way.
Fourth, get creative, be an artist and comedian that knows and teaches money. It won’t always be funny, not every video or piece of writing will be hilarious, but I’m committed to being in play, telling more jokes and laughing along the way.
Laughter is medicine.
Cliché, but at least somewhat true. Having fun provides energy. Enjoying the process along the way is inevitable with intentional life design.
So what’s your legacy? What do you love about life? What have you forgotten due to worry and pressure and trying to provide, grow, and profit?
I am here to lighten the financial burden by giving you tools, tactics, and frameworks to keep more of what you make without cutting back. To help you make more money with the strategies of investing in yourself. Giving you insights on how to discover your Investor DNA and become a better investor.
And most importantly, how to create the life you don’t want to retire from (and doing it with some fun).
In love and laughter,
Garrett
One thought on “Laugh Your Way to a Legacy that Really Matters”
Thank you!